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What Is Hillary Clinton Afraid Of?

Time columnist Joe Klein, who covered the Clintons in the ’90s and turned their story into the thinly fictionalized novel Primary Colors, thinks Clinton’s reticence is congenital, motivated by an innate fear of making mistakes in public. When Clinton thought she wasn’t being scrutinized, she relaxed and engaged as candidly and incisively as anyone he had ever interviewed. But on the record she would shut down, reciting bland talking points. “I don’t know why she doesn’t let her light shine,” Klein says. “In my experience, Hillary’s really hurt herself in the press by being too cautious. It really undersells all that hard work she does.”

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Back in the 1990s, her staff urged her to cozy up with an established class of top female reporters whose personal struggles in a male-dominated town mirrored Clinton’s own. Caputo, for example, in 1995, singled out three prominent female network correspondents for the Hillary treatment—ABC’s Ann Compton; Claire Shipman, then with CNN; and NBC’s Andrea Mitchell, whom Caputo described as “very aggressive and a very good reporter.” The proposed charm offensive—revealed as part of a Clinton Presidential Library document dump earlier this year—proceeded in a typical fits-and-starts fashion, according to the reporters.

The problem took on more urgency as Clinton transitioned from first lady to New York Senate candidate in 1999, fresh out of the Lewinsky debacle, when Clinton had blamed the media for smarmy allegations about her husband that turned out to be true. “Don’t be defensive,” Grunwald counseled Clinton at the time in another memo. “Look like you want the questions: The press is obviously watching to see if they can make you uncomfortable or testy. … Look for opportunities for humor. It’s important that people see more sides of you, and they often see you only in very stern situations.”

Clinton, liberated from the White House fishbowl, was no natural on the campaign trail, but dealing with the press on a day-to-day basis gave her a sense of confidence she’d never had in her husband’s shadow, especially once she won an election in her own right and moved into the Senate. Sotto voce, she even set out to improve her relationship with conservative media mogul Rupert Murdoch. Her 2000 campaign communications chief, Howard Wolfson, served as a back-channel emissary between the Clinton and Murdoch camps in his capacity as a strategic adviser to Murdoch’s News Corp. in its long-running battle with Nielsen over the ratings company’s viewer-tracking practices. Clinton herself made nice with the New York Post, Murdoch’s sharp-knifed right-wing tabloid. She cultivated a friendly rapport with Vince Morris, author of the paper’s “Hillary Watch,” column: When Morris’s wife delivered a daughter in 2002, Clinton wrote a letter directly to the child on Senate stationery.

“It was just a nice little gesture,” Morris recalls. “Hillary did a lot of things to sort of recognize my role—that I was not going away, it was going to be a permanent part of her reality as a senator, and that she might as well make the best of it.”

Cozying up to reporters didn’t come easily, but they appreciated the effort—even if it was jarring to have such a distant figure trying to connect. In 2006, Anne Kornblut, then a New York Times reporter, was trailing the senator around upstate New York when Clinton stopped her outside an event to ask her how someone named Eliza was doing.

The 2000s: A Politician is Born

By Margaret Slattery

The Senate years…

2007-2008: Clinton backers decry sexist coverage of the Democratic primary, blaming both liberals (Chris Matthews calling her a “she-devil”) and conservatives (Tucker Carlson: “When she comes on television, I involuntarily cross my legs”). In the thick of the campaign, 51 percent of Democratic primary voters say journalists are harsher on Clinton than other candidates, compared with 12 percent for Barack Obama.

2011: As secretary of state, Clinton appears on the cover of Time magazine and in a memorable accompanying shot that shows her sporting dark sunglasses and checking her BlackBerry aboard a military plane. The photo is the inspiration for the “Texts from Hillary” Tumblr, which helps shape her new, Internet-savvy image (and earns a response from Clinton herself: “ROFL @ ur tumblr!”).

2012-2013: In the heat of the presidential campaign, Republicans take to conservative radio and TV to lambaste Clinton for the deaths of U.S. Ambassador Chris Stevens and three other Americans in Benghazi, Libya, on her watch. At a January 2013 Senate hearing, Clinton’s agonized response to questions about how the Americans were killed—“What difference at this point does it make?”—goes viral.

2013: Approaching the end of her tenure at State, Clinton joins President Obama—her former campaign rival—for a fawning co-appearance on 60 Minutes, in which Obama says Clinton “will go down as one of finest secretary of states we’ve had” and calls her “one of the most important advisers that I’ve had on a whole range of issues” and a “strong friend.” Asked about her next move, Clinton demurs.

“It threw me. Eliza? Who is Eliza?” recalls Kornblut, who would go on to write Notes from the Cracked Ceiling about the 2008 campaign. “It was so out of context that it took me a moment to realize Clinton was asking about my college roommate, whose mother is the Clintons’ interior decorator. It was all the more surprising because Clinton had seemed so reluctant to forge any bonds with those of us who were following her around. Such moments were rare, and grew rarer as the [2008] campaign wore on, but when they happened, people wondered why she didn’t try to show that side of herself more often.”

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Her eight years in the Senate alsosaw the rise of the quintessential Clinton press handler, Philippe Reines, a singularly colorful figure in D.C. flack-dom who shares his boss’s contempt for the national political press. Unlike Clinton, he also dearly loves the hand-to-hand combat of reporter-wrestling, and proffers a detailed critique of journalistic practice.

“Individual reporters don’t matter as much as the way the industry behaves as a whole,” Reines told us over Diet Cokes at a Chinese restaurant in Washington, with a smiling photo of Hillary Clinton looking down approvingly from a nearby wall. “There’s an overall dynamic in place larger than any one person. The pressure to produce is so overwhelming that reporters are filing two, three times a day. The emphasis has completely shifted away from quality, to quantity and speed, and it’s come at the expense of accuracy and fairness. … Every single reporter I sit with bemoans the pressure to produce more and produce it faster, and acknowledges both come at the expense of fundamental editorial standards like getting it right.”

Nothing gets Reines as worked up as the notion that Clinton gets lousy press because she’s too secretive or defensive. “We’re not the ones breathing down your necks to crank out stories at the same rate as a factory assembly line,” he adds. “Things are a mess. … Can you honestly say that this is all about us? You’re not part of that problem? Listening to the media complain about how horrible we are to the media, you’d think it takes only one to tango.”

Over the years, Reines has been “fired” at least twice—once for breaking the no-staffer-profiles dictum, another after he slipped a nasty background quote into a Maureen Dowd column in the New York Times that invoked John McCain’s Hanoi imprisonment. When a furious Clinton ordered a subordinate to ax him after Dowd-gate, the staffer refused on the grounds that Clinton would hire him back a few days later.

Reines, like everyone else in Hillaryland, coveted a big role during the hopeful days leading into Clinton’s 2008 presidential campaign, but he was elbowed out by rivals.